Reaction of Hydrogen Bromide with Long Chain 1,2-Diols

The reactions of 1,2-hexadecanediol and 1,2-octadecanediol with hydrogen bromide in the presence of acetic anhydride have been investigated. The treatment of hydrogen bromide (48%) in acetic anhydride with 1,2-hexadecanediol gives mainly 1-bromo-2-acetoxy hexadecane (66%), 2-acetoxy hexadecanol (26%), and 1,3-hexadecanediol (8%). Similar products result from 1,2-octadecanediol. The structures of the products are based on combustion data, spectroscopic, and chemical evidences. The mechanism of the reaction has been discussed.